Investing in the best Chelsea boots is a smart way to put your best fashion foot forward this season.
Chelsea boots are a classic style that are most recognized for their ankle-skimming, close-fitting silhouette. Due to their sleek shape, they often feature an elastic side panel for ease of fit and movement and many Chelsea boots also feature front and back loop tabs—these are largely there to aid you in pulling your boots on.
A timeless silhouette, the Chelsea boot never really dates, which makes it a wardrobe essential in any footwear capsule wardrobe. A style you can wear season after season, the Chelsea boot is enjoying a fashion-high right now after making a reappearance on the runway and is firmly one of the big boot and autumn/winter shoe trends 2023 to watch out for.
While traditionally Chelsea boots have been quite a robust and practical piece of footwear, their recent fashion makeover has given them a new lease of life, spawning new and exciting iterations. From Chelsea boots with heels, to Chelsea boots with platform soles, this new crop of shapes promises a style for all tastes and occasions. Comfortable for walking but still stylish, the Chelsea boot is the piece of footwear to buy this season.
Where to shop for the best Chelsea boots
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- Clarks—Winner on price and quality, Clarks is one of the stalwarts of the British shopping landscape. Prices from $130 / £79
- Dr Martens—The boot that will never go out of style Dr Martens are enjoying somewhat of a fashion resurgence right now. Prices from $100 / £139
- Dune—Put your best fashion foot forward with Dune’s stylish Chelsea boots. Prices from $135 / £95
- Jones Bootmaker—Bootmakers by name, this is a good pitstop for well-priced, classic styles. Prices from $77 / £57
- Kurt Geiger—Best for fashion-led interpretations, Kurt Geiger retail Chelsea boots with an edge. Prices from $89 / £95
- RM Williams—They're on the pricier side, but you’re buying into R.M. Williams timeless quality. Prices from $495 / £375
- Russel and Bromley—A beautiful combination of fashion and quality, Russell and Bromley mix high fashion with wearability. Prices from £175
The best Chelsea boots as chosen by our style experts
Clarks is a heritage British brand and a name well trusted amongst UK shoppers. The shoe brand stocks everything from children’s to adult's shoes and is known for their quality and classic styles. While their selection of Chelsea boots is not vast, it does carry versatile silhouettes in a host of colors, meaning you can stock up on the basics to underpin your wardrobe. When it comes to styling a pair of Chelsea boots, there is no need to worry about 'what color suits me', but you should certainly think about what color clothing you have in your wardrobe and what shades of shoe you normally gravitate towards.
RRP: $130 / £89 | Sizes: US: 5-12 Medium, Wide / UK: 3-8 Standard | You can’t go wrong with classic black leather Chelsea boots. As these boots are quite short on the leg, pair with black opaque tights to elongate your pins. The clean frontage ensures these will style well under jeans and trousers.
RRP: $160 / £110 | Sizes: US: 4.5-10.5 Medium, Wide / UK: 3-8 Standard, Wide | With a slightly higher leg these chocolate brown Chelsea boots will be great with boho dresses in the spring. Chelsea boots by their nature are tight fitted, so this stretch panel offers a comfier fit.
RRP: $160 / £120 | Sizes: US: 5.5-10.5 Medium, Wide / UK: 3-8 Standard | Putting a new twist on the classic Chelsea boot style with a height boosting wedge, these Clarkford boots are great for those who want to tap into the trend without compromising on those all-important inches.
The home of the stompy boot, the Dr Martens Chelsea boot is an absolute classic. This simple shape of boot is universally loved and as the brand has seen a resurgence in popularity amongst the fashion crowd, one of their key styles, also known as 2976 has enjoyed frequent updates and fashion makeovers. While Dr Martens boots are traditionally leather, the brand has introduced Dr Martens vegan leather 2976's as well as using the faux leather across a number of other styles.
Generally quite a heavy boot, Dr Martens might not be the sartorial choice for every Chelsea boot lover, but while this hefty piece of footwear used to live on the fashion fringes, it is now firmly in the spotlight as one to invest in. Wear with everything from pretty midi dresses to the very best jeans for women.
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RRP: $140 / £139 | Sizes: US: 5-11 / UK: 3-9 | Dr Martens’ classic 2976 Chelsea boot gets a slick fashion makeover with a high shine patent finish. While a Dr Martens black boot is a statement piece of footwear that will go with pretty much anything, the patent finish makes this pair particularly special.
RRP: $150 / £149 | Sizes: US: 5-12 / UK: 3-13 | Go vegan with Dr Martens classic 2976 Chelsea boot now in faux leather. Taking note of the growing pushback against animal products in fashion, you can now buy into the Dr Martens craze with a soft and subtle, synthetic material.
RRP: $160 / £159 | Sizes: US: 5-11 / UK: 3-9 | Lined in faux-fur these stompy, chunky Chelsea boots will be super warm and protective. In a classic Dr Marten Chelsea boot style, they are lined in cream faux fur, keeping you stylishly cozy for the season ahead. Tuck in some skinny jeans for a casual outfit.
Dune London is a great destination for fashion-forward shoe options and with so many styles available across all footwear and handbag categories, you really will be spoilt for choice. With a mid to high-end price point, the boots can easily tip over the $100/£100 mark, but with such directional styles, you'll get both use and enjoyment out of Dune London pieces. While they might have London in the name, don't worry, this British brand ships all over the world too.
RRP: $140 / £99| Sizes: US: 5-10 / UK: 3-8 | The brogue detailing makes this boot particularly smart and great for teaming with tailored trousers and any of the best blazers for women. It's also available in two colorways.
RRP: $155 / £110 | Sizes: US: 5-10 / UK: 3-8 | Traditionally a flat boot, we're seeing more heeled Chelsea boots spring up at a host of retailers, meeting the demand for more trend-led pieces. This mid-block heel Chelsea boot is great for every day.
RRP: $225 / £160 | Sizes: US: 5-10 / UK: 3-8 | Camel is such a versatile color, working for all seasons. In winter team it with monochrome and khaki hues for a really earthy feel and in spring pair with summer florals for a fresh twist.
Jones Bootmaker, the clue is in the name. Another British heritage brand, Jones Bootmaker features a massive brand mix, from independents to more well-established, household names such as, Fly, Gabor, Karen Millen and Barbour. This means you can shop for lots of different labels all in one place and really compare styles, colors and prices. We love the range of classic Chelsea boots at Jones Bootmaker, they're the pieces you can keep in your wardrobe for years to come.
RRP: $196 / £99 | Sizes: US: 5-9 / UK: 3-7 | Sleek and streamlined, this longer-length Chelsea boot combines a thick-sole tread with the classic Chelsea boot silhouette. With leg-lengthening properties, the smooth leather insock will partner well with trousers, skirts, and dresses alike.
RRP: $134 / £99 | Sizes: US: 5-10 / UK: 3-8 | Part Chelsea boot, part ankle boot, these sleek boots will easily become a pair you reach for on repeat. Wear under jeans, with floral dresses, or matched with midi skirts. The slender toe will help to elongate your legs, while the elastic insert gives a comfortable fit.
RRP: $155 / £115 | Sizes: US: 5-10 / UK: 3-8 | A stylish alternative to black boots, you can wear these red-toned, brown boots all year through, as they’ll pair well with darker and lighter clothing. The higher up-the-leg finish means they’ll be fab with dresses and skirts too.
Kurt Geiger packs a real fashion punch when it comes to forward-thinking footwear. Taking classic silhouettes, such as the Cheslea boot and giving it an updated look for the season ahead. Perhaps taking some inspiration from some of the biggest jewelry trends 2022, Kurt Geiger have leaned into embellishment for the upcoming season. Kurt Geiger boots are there to get you noticed, so keep the rest of your outfit fairly muted to allow them to shine.
RRP: $95 / £89 | Sizes: US: 6-11 / UK: 3-8 | While these take inspiration from Chelsea boots, their rubberized finish makes them quite like a Wellington boot too. If you've shied away from chunky and uncomfortable wellies, then try a pair of these for rainy day style.
RRP: £139 | Sizes: UK: 3-8 | Chunky soles have played a big part in the Chelsea boots comeback story and this Kurt Geiger pair is a perfect example of that. The ribbed ankle gives a great level of comfort, while the main sole remains platformed and weighty.
RRP: $240 / £219 | Sizes: US: 6-10 / UK: 3-8 | A classic Chelsea boot but with a little more fashion, the gem-stoned ankle strap offers a fun and dressy finish. Secured with a buckle, the strap is removable too, offering you versatility for those days you want to go sans sparkle.
Originally crafted for the Australian outback, these top-quality Chelsea boots can certainly handle you pounding the pavements. Established in 1932, R.M. Williams have become world-renowned for their high-end, but practical footwear. With a tradition in riding boots, these are a fairly big investment piece but one you can buy knowing you'll still be wearing them for years to come.
RRP: $495 / £375 | Sizes: US: 5-11 / UK: 2.5-8.5 | These Chelsea boots offer a classic example of how to wear boots with jeans. With a narrowed toe silhouette, pair with straight-legged or wide-legged jeans and allow the toe to just peep out from beneath the hem.
RRP: $495 / £375 | Sizes: US: 5-11 / UK: 2.5-8.5 | Masterfully crafted from a single piece of leather, these are a truly gorgeous pair of heeled, black leather Chelsea boots. Sharp and sophisticated, the sole has been constructed so that it is easily replaceable whenever you need to.
RRP: $545 / £400 | Sizes: US: 5-11 / UK: 2.5-8.5 | Adding a little frivolity to proceedings, Chelsea boots aren't just for work. These streamlined metallic leather boots with pointed toe will be great with dressier ensembles too. Pair with your best sequins for a night out.
This British luxury shoe brand perfectly combines directional design with timeless silhouettes. Much like a Burberry trench coat, Russell and Bromley shoes and boots make for a great investment purchase and are synonymous with luxury and craftsmanship. If you're happy to splash out on some new Chelsea boots, think about color and silhouette to ensure you get the most wear out of them. Most styles will work just as well with dresses as with jeans, but opt for neutral brown or black for maximum versatility.
RRP: £175 (UK only) | Sizes: UK: 3-8 | The best of both, this Chelsea boot meets sneaker, gives you maximum comfort and style in one hit. Offering a sports-luxe aesthetic, with easy pull-on tabs and a striking monochromatic finish, this style of boot will go with everything. If you've been wondering what to wear with black jeans, you've met your match.
RRP: £225 (UK only) | Sizes: UK: 3-8 | This camel hue is such a gorgeous update for spring and softer than black for warmer weather. While the boot itself is quite weighty looking, you can easily pretty up this stompy silhouette with any of the best midi dresses for a take that's fresh, feminine, and most importantly, practical and comfy.
RRP: £295 (UK only) | Sizes: UK: 3-6 | Made in Italy, this super sleek boot is one of the sharpest pair of Chelsea boots we have seen this season. A totally classic version of this much-loved style, these slightly pricier boots are certainly a pair that you can wear season after season. Keep well-polished, so you can enjoy these boots for years to come.
How to style Chelsea boots
If you've mastered how to style knee-high boots, you'll be pleasantly surprised to know that styling the best Chelsea boots is not that different.
In previous years shorter boots were very much relegated to only being worn with boot cut jeans, but fashion rules, as they say, are made to be broken and in recent years, most decrees have been thrown out entirely.
While Chelsea boots are traditionally ankle or sometimes a little higher, they're now universally worn with pretty much everything. Making them a really strong style to invest in this season.
Whether you're wondering what to wear with a pleated skirt, or searching for the best boots to wear with your favorite mom jeans, a good pair of neutral Chelsea boots could solve a multitude of fashion dilemmas.
The best Chelsea boots for women can be styled with full skirts, worn poking out from under trousers, pulled over jeans and even styled as part of your favorite leggings outfits.
If you're worried about whether a Chelsea boot is as leg lengthening as the best knee-high boots, utilize accessories to help boost your pins. Stylists know that the more places your cut your silhouette with different hemlines, the shorter your torso and legs appear. If you're wearing your Chelsea boots with shorter skirts or dresses, wear a pair of opaque tights that match the color of your chosen boot. This will avoid an extra line on your silhouette and boost the appearance of your height in seconds.
How to care for Chelsea boots
As Chelsea boots are short, they're wearable right through til spring and will still look cute with shorter summer dresses and shorts in the very early days of summer. But when it's time to swap boots for sandals, you need to make sure your boots are well looked after to get maximum wear and value from them.
Just like the best winter coats, at the end of the season make sure to pack your boots away in a good condition so that they'll be ready for the autumn. This means giving them a good clean and polish and seeing if any repairs need to be done. Get shoes resold and reheeled ready for the next season.
Making this part of your wardrobe routine at the end of a season will ensure you can keep your clothes, shoes and boots in good health and you can wear them for as long as you want. And when you're bored of them, they'll be such a good enough condition, you can even investigate how to sell clothes online and possibly make enough money to fund your next wardrobe.
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